Method of controlling manure-breeding insects

ABSTRACT

A method of controlling manure-breeding insects which comprises orally administering to a warm-blooded animal an insecticidally-effective amount of a compound of the formula ##STR1## wherein each X substituent is individually chosen from the group consisting of Cl, F, CH 3 , and OCH 3  ; R is a halogenated methyl or ethyl group; and Y represents sulfur or oxygen.

BACKGROND OF THE INVENTION

This invention is concerned with animal husbandry and in particular, isconcerned with the control of manure-breeding insects, which are knownto be vectors in the transmission of various animal diseases.

One advantage of the method of the present invention is that thecompounds utilized therein retain their insecticidal properties afterpassing through the digestive system of the treated animals. Thus, theapplication of the insecticidal compounds can be centralized and thenumber of applications of these compounds can be reduced. This is adistinct advantage when there are a large number of animals to betreated. The method of the present invention is further advantageous inthat the insecticides, when used in "feed thru" applications, will belocalized directly in the animal's manure where they will be mosteffective in the control of manure-breeding insects.

DESCRIPTION OF THE INVENTION

These and other advantages as will become apparent from the followingspecification and appended claims are achieved, according to the presentinvention's method of controlling manure-breeding insects, by orallyadministering to a warm-blooded animal an insecticidally-effectiveamount of a compound of the formula ##STR2## wherein each X substituentis individually chosen from the group consisting of Cl, F, CH₃, and OCh₃; R is a halogenated methyl or ethyl group; and Y represents sulfur oroxygen.

Compounds in accordance with the above formula are alternativelyreferred to herein as "active compounds" .

Examples of active compounds in accordance with the above formula whichare utilized in the method of the present invention are:

2,6-Dichloro-N-(((4-(trifluoromethoxy)phenyl)-amino)carbonyl)benzamide(hereinafter referred to as Compound 1);

2,6-Difluoro-N-(((4-(trifluoromethoxy)phenyl)-amino)carbonyl)benzamide(Compound 2);

2,6-Dichloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)-phenyl)amino)carbonyl)benzamide(Compound 3);

2,6-Difluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)-phenyl)amino)carbonyl)benzamide(Compound 4);

2,6-Dimethoxy-N-(((4-(1,1,2,2-tetrafluoroethoxy)-phenyl)amino)carbonyl)benzamide(Compound 5); and

2,6-Difluoro-N-(((4-(1,1-difluoro-2,2-dichloroethylthio)phenyl)amino)carbonyl)benzamide(Compound 6).

The active compounds which are utilized in the method of the presentinvention are highly effective in controlling manure-breeding insectssuch as houseflies, face flies, and hornflies. These compounds may beadministered to the warm-blooded animals in admixture with their feed ordrinking water. Furthermore, the active compounds utilized in thepresent invention may be administered in the form of tablets, pills,capsules or the like. These active compounds may be admixed withpharmaceutically-acceptable carriers for use in animals, however, theyare usually used as a component in the animal feed or drinking water.

The insecticidally-effective dosage desirable for effective use ofpreparations containing active compounds will naturally depend onvarious factors such as the active compound or compounds chosen and theform of preparation. Moreover, the activities of the compounds againstdifferent insects will vary from compound to compound. It is onlynecessary that one or a combination of the compounds be orallyadministered in a sufficient amount so as to make possible theapplication of an insecticidally-effective or inactivating dosage.Generally, one or a combination of the active compounds can be orallyadministered to a warm-blooded animal, especially a ruminant, at a dailydosage of from about 0.01 to about 1 milligram of active compound perkilogram of animal body weight.

When administered to poultry, an effective dosage rate will generallyrange from about 3 parts to about 50 parts of active compound permillion parts of poultry feed.

These compounds may be effectively administered to warm-blooded animals,especially ruminants, dogs, horses, swine and poultry.

EXAMPLES

The examples which follow should not be construed as limitations uponthe overall scope of the invention.

EXAMPLE 1

A calf weighing 187 kilograms was, for 5 days, administered Compound 1daily in its feed at a dose rate of 0.5 milligrams per kilogram of bodyweight. Thus, the calf was fed 93.5 milligrams of the compound everyday. On the fourth, fifth and sixth day of the test, manure samples werecollected from the treated animal and frozen to kill any wild insectlarvae that may have been present. The samples were thawed and wereseeded with equal amounts of eggs from colony strains of hornflies andhouseflies. Control samples were also similarly seeded at that time. Thesamples were incubated at 80° F for a period of time sufficient to allowthe eggs to hatch.

The percent control was determined by counting the number of normaladult flies that hatched from the treated samples and comparing thisfigure with the number of flies that hatched from the untreated(control) samples. It was determined that there was, in the treatedsamples, 100% control of both houseflies and hornflies. The abovecompound was similarly tested at other dose rates. The percent controlof hornflies and houseflies at these dose rates are set forth in Table1.

                  TABLE 1                                                         ______________________________________                                        DOSE RATE                                                                     (Milligrams per                                                               Kilograms of                                                                             Percent Control of                                                 Body Weight)                                                                             Hornflies     Houseflies                                           ______________________________________                                        0.1        98            77                                                   0.05       99            0                                                    0.01       77            0                                                    ______________________________________                                    

EXAMPLE 2

Using the procedure of Example 1, Compounds 2 and 3 were likewise testedfor housefly and hornfly control at various dose rates. The results ofthese tests are set forth in Table 2.

                  TABLE 2                                                         ______________________________________                                        DOSE RATE                                                                     (Milligrams per                                                               Kilogram of     Percent Control of                                            Compound                                                                              Body Weight)                                                                              Hornflies  Houseflies                                     ______________________________________                                        2       0.1         100        100                                            2       0.05        100        85                                             2       0.025       100        25                                             2       0.01        99         0                                              3       0.5         99         60                                             ______________________________________                                    

EXAMPLE 3

Using generally similar procedures, Compounds 4, 5 and 6 were tested forhornfly control at various dose rates. The results of these tests areset forth in Table 3.

                  TABLE 3                                                         ______________________________________                                                   DOSE RATE     Percent                                                         (Milligrams per                                                                             Control                                                         Kilogram of   of                                                   Compound   Body Weight)  Hornflies                                            ______________________________________                                        4          0.1           100                                                  5          0.1           98                                                   6          0.05          85                                                   ______________________________________                                    

EXAMPLE 4

Compounds 1 and 2 were similarly screened as feed thru insecticidesagainst the larvae of face flies. Table 4 sets forth the results ofthese screens.

                  TABLE 4                                                         ______________________________________                                        Percent Control of Face Fly Larvae                                                       Dose Rate     Percent                                              Compound   (mg/kg/day)   Control                                              ______________________________________                                        1          .01           69.5                                                 1          .05           100                                                  2          .01           100                                                  2          .05           99.2                                                 ______________________________________                                    

EXAMPLE 5

Compound 1 was added to chicken feed at the rate of 5 parts of compoundper million parts of feed. Samples of chicken droppings were collectedand, after being frozen and thawed, were seeded with larvae fromDDT-resistant and DDT-susceptible strains of houseflies. Control sampleswere also seeded. The tests were repeated at 1 and 3 parts of compoundper million parts of feed. Table 5 sets forth the percent control of thesusceptible and resistant strains at the indicated concentrations.

                  TABLE 5                                                         ______________________________________                                        Percent Control of Housefly Larvae Using Compound 1                                    Parts of Compound 1 Per Million Parts Feed                           Strain     5          3           1                                           ______________________________________                                        Resistant  100         90          0                                          Susceptible                                                                              100        100         50                                          ______________________________________                                    

The test was repeated using Compound 2, with the results being set forthin Table 6.

                  TABLE 6                                                         ______________________________________                                        Percent Control of Housefly Larvae Using Compound 2                                    Parts of Compound 2 Per Million Parts Feed                           Strain     5          3           1                                           ______________________________________                                        Resistant  100         99         50                                          Susceptible                                                                              100        100         90                                          ______________________________________                                    

PREPARATION OF THE ACTIVE COMPOUNDS

The active compounds utilized in the present invention's method can beprepared by reacting an appropriate benzoyl isocyanate derivative withan appropriate anisidine or phenetidine derivative.

The reaction is carried out by contacting the reactants together inequimolar proportions in the presence of a solvent at a reactiontemperature which, at atmospheric pressure, may vary from 0° C to theboiling point of the solvent used. Examples of suitable solvents arearomatic hydrocarbons such as benzene or xylene, chlorinatedhydrocarbons such as chloroform, methylene chloride or ethylene chlorideor other inert solvents such as acetonitrile.

Following the completion of the reaction (generally lasting from about0.5 to about 24 hours), the mixture is cooled and the precipitatedproduct is collected by filtration or other suitable techniques. Thisproduce is usually washed with a solvent such as hexane, and dried. Theresulting crude product may be further purified, if desired, byrecrystallization from a solvent such as aqueous acetic acid or by otherpurification procedures.

What is claimed is:
 1. A method of controlling manure-breeding insectswhich comprises orally administering to a warm-blooded animal aninsecticidally-effective amount of a compound of the formula ##STR3##wherein each X substituent is individually selected from the groupconsisting of Cl, F, CH₃, and OCH₃ ; R is a halogenated methyl or ethylgroup; and Y is sulfur or oxygen.
 2. The method of claim 1 wherein thecompound is2,6-Dichloro-N-(((4-(trifluoromethoxy)phenyl)amino)-carbonyl)benzamide.3. The method of claim 1 wherein the compound is2,6-Difluoro-N-(((4-trifluoromethoxy)phenyl)amino-carbonyl)benzamide. 4.The method of claim 1 wherein the compound is2,6-Difluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)-amino)carbonyl)benzamide.5. The method of claim 1 wherein the compound is2,6-Dichloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)-amino)carbonyl)benzamide.6. The method of claim 1 wherein the compound is2,6-Dimethoxy-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)-amino)carbonyl)benzamide.7. The method of claim 1 wherein the compound is2,6-Difluoro-N-(((4-(1,1-difluoro-2,2-dichloroethylthio)-phenyl)amino)carbonyl)benzamide.